US4622038A - Low residue fiber spin finishes - Google Patents

Low residue fiber spin finishes Download PDF

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Publication number
US4622038A
US4622038A US06/695,308 US69530885A US4622038A US 4622038 A US4622038 A US 4622038A US 69530885 A US69530885 A US 69530885A US 4622038 A US4622038 A US 4622038A
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United States
Prior art keywords
fiber
sum
less
methyl
residue
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US06/695,308
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English (en)
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Robert B. Login
Michael J. Anchor
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BASF Corp
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BASF Corp
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Priority to US06/695,308 priority Critical patent/US4622038A/en
Priority to EP86100642A priority patent/EP0189804A3/de
Priority to CA000500413A priority patent/CA1239505A/en
Assigned to BASF CORPORATION, A CORP. OF DE. reassignment BASF CORPORATION, A CORP. OF DE. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: ANCHOR, MICHAEL J., LOGIN, ROBERT B.
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/165—Ethers
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions

Definitions

  • the subject invention relates to fiber spin finishes containing fiber lubricants which produce low residue levels. More particularly, the invention relates to the use of polyoxyalkylene polyether diols based upon 2,2-dialkyl-1,3-propanediols as spin finish lubricant additives.
  • Fiber finishing compositions are a necessary part of modern, high speed synthetic fiber manufacture. Virtually all operations performed on the fibers following their being spun from the melt require the presence of suitable fiber finishes to prevent snarling and breaking, thus enabling higher fiber throughput.
  • a quality fiber finish must provide several, often conflicting qualities. For example, the fiber finish must qualify both the interaction between the fiber and the machinery on which it is processed, and also the interactions among the fiber filaments themselves. This property is usually termed "lubricity" although in reality the change in the interactions caused by the fiber lubricant may sometimes result in a desirable increase in friction as well as the decrease in friction ordinarily associated with the term "lubricant.”
  • the fiber finish composition In addition to its "lubricant" qualities, the fiber finish composition must control static electricity generated during fiber processing. Generally, ionic organic compounds such as synthetic phosphate and sulfonate detergents are useful as antistats and are added to the fiber finish composition for this purpose.
  • the fiber finishes are generally applied in the form of an aqueous emulsion by any one of several methods including the use of kiss rolls, sprayers, baths and squeeze rollers, and grooved ceramic guides and metering pumps.
  • surfactants such as fatty alcohol oxyethylates and nonylphenol oxyethylates are generally necessary.
  • a suitable fiber finish must also be easily removable from the fiber or yarn so as not to interfere with subsequent operations such as dyeing and bleaching. Furthermore, since the finish performs its intended functions only on the outside of the fiber, it should not be easily absorbed into the fiber proper. Penetration of the fiber lubricant into the fiber increases the quantity of lubricant required during the finishing operation and, in addition, may cause undesirable changes in the physical properties of the fibers themselves.
  • the fiber throughput associated with modern fiber finishing operations have increased, the demands placed upon the fiber finish, especially the lubricant which comprises a major portion of the finish, have increased as well.
  • drawing and twisting operations for example, the fiber is drawn across a heater plate, hot draw roll or heating pin in order to raise the temperature of the fiber to the plastic deformation stage.
  • the fibers then undergo stretching, twisting, tangling, or a combination of these operations.
  • the cooled, stretched fiber generally has a much higher tensile strength than the raw fiber. If the fiber has been twisted or tangled in addition to being stretched, it retains these modifications, thus imparting improved feel, fabric cover, recovery from deformation and other properties felt desirable by the textile industry.
  • the fibers may also be textured by processes such as stuffer-tube crimping and edge crimping. These processes also require the fibers to be heated to the same relatively high temperatures as for drawing and twisting, generally in the neighborhood of 190° C. or higher.
  • the temperature of the heating elements must be increased as well in order for the faster moving fibers to be heated to the requisite processing temperatures.
  • Fiber processing machinery is capable of running at speeds in excess of 1000 m/min.
  • the primary heater plate temperature must be maintained at temperatures of 250° C. or higher to enable sufficient heat transfer to the fast moving fibers.
  • prior art lubricants resinify causing a rough resinous coating to cover the heater plate. This buildup of resinous coating on the heater plate not only causes decreased thermal transfer from the plate to the fiber but, more importantly, is a primary cause of broken filaments.
  • Prior art lubricants include mineral oils and waxes, fatty acid esters such as butyl stearate, vegetable oils and waxes, neoalcohol esters, silicones, and polyoxyalkylene polyethers.
  • the fiber lubricants yielding the least resinous buildup for high speed fiber processing for example, are the propylene oxide/ethylene oxide block copolymers such as PLURONIC® L-31 block copolymer surfactant. In pan tests at 210°, for example, PLURONIC® L-31 typically has less than 3 percent by weight unvolatized residue after four hours and less than 1 percent after 24 hours.
  • fiber lubricants which are polyoxyalkylene glycols based upon 2,2-dialkyl-1,3-propanediols as initiator molecules. These products correspond to the formula: ##STR1## wherein R is the alkylene portion of a 2 to 4 carbon oxyalkylene residue, m and n are integers such that the average value of the sum (m+n) is less than about 30, and R 1 and R 2 are individually selected from the group consisting of alkyl radicals having from 1 to 8 carbon atoms. These polyoxyalkylene glycols exhibit exceptionally low residues when used in fiber processing operations.
  • the fiber lubricants of the subject invention are produced by the addition polymerization of one or more oxiranes or other cylic ethers onto an initiator molecule which is selected from the group consisting of 2,2-dialkyl-1,3-propanediols.
  • suitable indicator molecules include 2,2-dimethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2,2-dipropyl-1,3-propanediol, 2,2-diisopropyl-1,3-propanediol, 2,2-dibutyl-1,3-propanediol, and 2-ethyl-2-methyl-1,3-propanediol.
  • the 2,2-dialkyl-1,3-propanediol initiators are available commercially or may be synthetized by procedures familiar to the organic chemist, for example, by the reaction of suitably substituted aldehydes in an aldol condensation or by the acid catalyzed ring opening of suitably substituted oxetanes.
  • the preparation of 2-alkyl-2-methyl-1,3-propanediols, for example, is the subject of U.S. Pat. No. 4,097,540 wherein substituted acroleins (acrylaldehydes) are reacted with formaldehyde, followed by reduction.
  • Preferred 2,2-dialkyl-1,3-propanediols are 2,2-dimethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, and 2-ethyl-2-methyl-1,3-propanediol. Especially preferred because of its ready availability and low cost is 2,2-dimethyl-1,3-propanediol.
  • the 2,2-dialkyl-1,3-propanediol initiator is oxyalkylated by means of a ring-opening condensation polymerization with one or more cyclic ethers in the presence of either a basic catalyst or a Lewis acid catalyst.
  • Basic catalysis is preferred.
  • Suitable basic catalysts are alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, and barium hydroxide.
  • Preferably used are sodium hydroxide and potassium hydroxide.
  • Alkali metal alkoxides such as sodium methoxide and potassium methoxide are also suitable.
  • the amount of catalyst required is from 0.01 percent to 2 percent by weight of the initiator charge.
  • Suitable cyclic ethers include the oxiranes, such as oxirane, methyloxirane, 1,2-dimethyloxirane, and ethyloxirane. Methyloxirane is especially preferred.
  • oxiranes such as oxirane, methyloxirane, 1,2-dimethyloxirane, and ethyloxirane.
  • Methyloxirane is especially preferred.
  • oxetane and tetrahydrofuran are also suitable for the practice of the invention. When the latter are used, Lewis acid catalysis is preferred.
  • Suitable Lewis acid catalysts are aluminum chloride and boron trifluoride etherate.
  • the oxyalkylation may be performed by addition of only one cyclic ether, by addition of mixtures of cyclic ethers, or by alternating addition of individual cyclic ethers or their mixtures. Generally, from 1 to about 60 moles of cyclic ether per mole of initiator may be utilized. Preferably, from 2.5 to about 12 moles of cyclic ether is added.
  • the most preferred embodiments of the subject invention are those fiber lubricants prepared by the ring-opening condensation polymerization of methyloxirane onto 2,2-dimethyl-1,3-propanediol as the initiator.
  • These polyoxyalkylene polyethers give uniquely low residue values in pan tests.
  • These lubricants may be used alone, or preferably with other lubricants such as those having lower coefficients of friction but higher levels of residue in fiber spin finishing operations.
  • the lubricants are also advantageously utilized either alone or in admixture with other fiber lubricants in the processing of heavier denier fibers and yarns as, for example, those utilized in tire cord fabrics.
  • the examples which follow serve to illustrate the invention but do not serve to limit it in any way.
  • a 2.5 mole methyloxirane adduct of 2,2-dimethyl-1,3-propanediol was prepared.
  • a one-gallon stainless steel autoclave was charged with 833 grams (8.0 mole) of 2,2-dimethyl-1,3-propanediol and 8.4 grams (0.067 mole) of 45 percent by weight aqueous potassium hydroxide. Under a blanket of nitrogen, the mixture was heated to 130° C., and stripped free of water. The pressure was adjusted to 0 to 3 psig with nitrogen and 1160 grams (20.0 mole) of methyloxirane was added at the rate of 200 to 250 g/hr. After the last of the methyloxirane had been added, the mixture was held for three hours to insure complete reaction.
  • the crude mixture was then cooled to 80° C. and 57 g magnesium silicate was added. After one hour of stirring, the crude product was filtered and volatiles removed in vacuo.
  • the clear, water-white product had a hydroxyl number of 463 (450 calculated), an aqueous cloud point at 1 percent concentration of 100° C., a surface tension at 0.1 percent concentration of 55.1 dynes/cm, and a viscosity of 234 SUS at 100° F. (37.8° C.).
  • a pan test of the lubricant at 210° C. yielded only 0.06 percent residue after 24 hours. The lubricant was tested on the Rothchild F-meter where a coefficient of friction of 0.47 relative to butyl stearate (0.35) was obtained.
  • a 10.4 mole methyloxirane adduct of 2,2-dimethyl-1,3-propanediol was prepared.
  • the procedure of Example 1 was followed, with an initial charge of 458 grams of 2,2-dimethyl-1,3-propanediol.
  • Aqueous 45 percent potassium hydroxide, 12.1 grams was added as catalyst, the water stripped, and was followed by addition of a total of 2330 grams of methyloxirane, of which 100 grams was vented after a reaction period of approximately 15 hours, including the three hour holding period.
  • the lubricity of the product was measured on the Rothchild F-meter.
  • the coefficient of friction, relative to butyl stearate, was 0.50.
  • Two pan tests of the product conducted at 210° showed 0.007 percent and 0.000 percent residue after 24 hours, respectively.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US06/695,308 1985-01-28 1985-01-28 Low residue fiber spin finishes Expired - Lifetime US4622038A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US06/695,308 US4622038A (en) 1985-01-28 1985-01-28 Low residue fiber spin finishes
EP86100642A EP0189804A3 (de) 1985-01-28 1986-01-18 Faserspinnveredlungszusammensetzung mit niedrigem Restgehalt
CA000500413A CA1239505A (en) 1985-01-28 1986-01-27 Low residue fiber spin finishes

Applications Claiming Priority (1)

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US06/695,308 US4622038A (en) 1985-01-28 1985-01-28 Low residue fiber spin finishes

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EP (1) EP0189804A3 (de)
CA (1) CA1239505A (de)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4859350A (en) * 1986-05-05 1989-08-22 Hoechst Celanese Corp. Viscosity regulators for water-based spin finishes
US4915855A (en) * 1986-05-05 1990-04-10 Hoechst Celanese Corp. Viscosity regulators for water-based spin finishes
US5049311A (en) * 1987-02-20 1991-09-17 Witco Corporation Alkoxylated alkyl substituted phenol sulfonates compounds and compositions, the preparation thereof and their use in various applications
US5466406A (en) * 1992-12-11 1995-11-14 United States Surgical Corporation Process of treating filaments
US6133226A (en) * 1996-01-19 2000-10-17 Lever Brothers Company, Division Of Conopco, Inc. Non-cationic systems for dryer sheets
US6296936B1 (en) 1996-09-04 2001-10-02 Kimberly-Clark Worldwide, Inc. Coform material having improved fluid handling and method for producing
US6300258B1 (en) 1999-08-27 2001-10-09 Kimberly-Clark Worldwide, Inc. Nonwovens treated with surfactants having high polydispersities
RU2178031C1 (ru) * 2000-07-14 2002-01-10 Ивановский государственный химико-технологический университет Композиция для приготовления состава для авиважной обработки шерстяных, полиэфирных волокон и их смесей
JP3258724B2 (ja) 1991-10-19 2002-02-18 クラリアント・ゲゼルシヤフト・ミト・ベシユレンクテル・ハフツング 生分解性紡糸仕上げ剤
CN106397134A (zh) * 2016-08-31 2017-02-15 浙江皇马科技股份有限公司 一种双羟丙基新戊二醇醚的制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4957648A (en) * 1987-08-06 1990-09-18 The Lubrizol Corporation Spin fiber lubricant compositions

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3036118A (en) * 1957-09-11 1962-05-22 Wyandotte Chemicals Corp Mixtures of novel conjugated polyoxyethylene-polyoxypropylene compounds
US4110227A (en) * 1977-09-19 1978-08-29 Basf Wyandotte Corporation Oxidation stable polyoxyalkylene fiber lubricants

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3370056A (en) * 1963-04-04 1968-02-20 Takeda Chemical Industries Ltd Production of polyoxyalkylene ethers
GB1482963A (en) * 1974-09-06 1977-08-17 Shell Int Research Process for oiling staple fibre
US4288331A (en) * 1979-06-13 1981-09-08 Shell Oil Company Lubricating compositions for primary backing fabrics used in the manufacture of tufted textile articles
JPS60215873A (ja) * 1984-04-06 1985-10-29 竹本油脂株式会社 ポリエステル又はポリアミド繊維糸の紡糸油剤用組成物

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3036118A (en) * 1957-09-11 1962-05-22 Wyandotte Chemicals Corp Mixtures of novel conjugated polyoxyethylene-polyoxypropylene compounds
US4110227A (en) * 1977-09-19 1978-08-29 Basf Wyandotte Corporation Oxidation stable polyoxyalkylene fiber lubricants

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4859350A (en) * 1986-05-05 1989-08-22 Hoechst Celanese Corp. Viscosity regulators for water-based spin finishes
US4915855A (en) * 1986-05-05 1990-04-10 Hoechst Celanese Corp. Viscosity regulators for water-based spin finishes
US5049311A (en) * 1987-02-20 1991-09-17 Witco Corporation Alkoxylated alkyl substituted phenol sulfonates compounds and compositions, the preparation thereof and their use in various applications
JP3258724B2 (ja) 1991-10-19 2002-02-18 クラリアント・ゲゼルシヤフト・ミト・ベシユレンクテル・ハフツング 生分解性紡糸仕上げ剤
US5466406A (en) * 1992-12-11 1995-11-14 United States Surgical Corporation Process of treating filaments
US6133226A (en) * 1996-01-19 2000-10-17 Lever Brothers Company, Division Of Conopco, Inc. Non-cationic systems for dryer sheets
US6296936B1 (en) 1996-09-04 2001-10-02 Kimberly-Clark Worldwide, Inc. Coform material having improved fluid handling and method for producing
US6300258B1 (en) 1999-08-27 2001-10-09 Kimberly-Clark Worldwide, Inc. Nonwovens treated with surfactants having high polydispersities
RU2178031C1 (ru) * 2000-07-14 2002-01-10 Ивановский государственный химико-технологический университет Композиция для приготовления состава для авиважной обработки шерстяных, полиэфирных волокон и их смесей
CN106397134A (zh) * 2016-08-31 2017-02-15 浙江皇马科技股份有限公司 一种双羟丙基新戊二醇醚的制备方法
CN106397134B (zh) * 2016-08-31 2018-11-27 浙江皇马科技股份有限公司 一种双羟丙基新戊二醇醚的制备方法

Also Published As

Publication number Publication date
EP0189804A2 (de) 1986-08-06
CA1239505A (en) 1988-07-26
EP0189804A3 (de) 1988-08-03

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